Robert Wilson’s first real job was delivering the Toronto Star so it was a natural for the guidance counsellor, who also grew up reading the newspaper, to look to the Star’s Santa Claus Fund when he wanted to give back.

But after delivering gift boxes with his friend Trudy Lingham on Saturday, the head of student services at a Peel high school says he gained something too.

“Both of us lead very busy lives because our jobs are intense,” says Wilson, who works at Glenforest Secondary School in Mississauga. “What it did was to give us a time frame to drive around and talk and reflect on what we were doing. And slow down,” says Wilson. “And that part of it was fun.”

It was also a challenge, one that Wilson likened to the Amazing Race, the task-oriented reality television show that has competitors travelling around the world.

Volunteers at one of the fund’s distribution centres loaded up Wilson’s Ford “sled” with about 40 boxes on Saturday, each labeled with the address of the recipient.

Wilson said he had to get out of the car and use his Smartphone to take photos of the address on each box in the trunk and then return to the warmth of the front seat to plot out a path using Google or Lingham’s map book.

“We’re out there together. It was a challenge because we wanted to make sure (the recipients) got that parcel,” said Wilson, who would save time by figuring out the route while Lingham was delivering a box. “And it was fun meeting the different people,” he said. One man invited the pair in for tea, but they declined because they wanted to get as many boxes delivered as possible.

Wilson says the whole experience was an eye-opener, despite the fact that he is no stranger to need.

“That’s not the world we revolve in on a daily basis,” said Wilson. “Having said that, I see a lot of it because I’m in a high school and a lot of our students are in that situation. But I don’t show up on their doorsteps.”

The guidance counselor started up a food bank last year outside his office and has been collecting from staff to run a secret elf program for students for seven years.

“If we know the family is struggling we may give (a student) a $25 gift certificate to a store like Loblaws,” said Wilson. “They go home and the family can share it.”

Wilson said he liked delivering the boxes so much that he has already signed up for next year.

Volunteers begin packing boxes around the end of September. The packed boxes start going out to depots around the third week of November and home deliveries begin as early as Nov. 30.